YAROSH et al.
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1
2-methylimidazole (1) and 4.04 mmol of (iodomethyl)-
silane 2a, 2c, or 2d was stirred for 3 h at 100–120°C
until the initial (iodomethyl)silane disappeared (ac-
cording to the 1H and 13C NMR data). The mixture was
cooled to room temperature, 20 mL of acetone was
added, and the precipitate was filtered off, washed with
acetone and diethyl ether, and dried. The filtrate con-
taining triiodide 4 or 6 was evaporated, and the residue
was purified by chromatography in a 10 ×900-mm
column charged with silica gel (MN Kieselgel 60,
0.063–0.2 mm) using acetone as eluent.
Rf 0.87 (acetone). H NMR spectrum (acetone-d6), δ,
ppm: 0.51 s (12H, MeSi), 2.41 s (3H, Me), 4.17 s (4H,
CH2N), 7.38 s (2H, 4-H, 5-H), 7.59 m (5H, Ph).
13C NMR spectrum (acetone-d6), δC, ppm: –4.34
(MeSi), 10.88 (Me), 39.69 (CH2N), 118.49 (C4, C5);
123.14, 129.04, 131.03, 134.64 (Ph); 141.48 (C2).
15N NMR spectrum (acetone-d6): δN –204.8 ppm.
29Si NMR spectrum (acetone-d6): δSi –1.9 ppm. Found,
%: C 34.72; H 4.14; I 49.72; N 4.05; Si 6.91.
C22H31I3N2Si2. Calculated, %: C 34.75; H 4.11;
I 50.07; N 3.68; Si 7.39.
2-Methyl-1,3-bis[(1-methylsilolan-1-yl)methyl]-
3,3,5,5,10-Pentamethyl-4-oxa-7-aza-1-azonia-3,5-
disilabicyclo[5.2.1]deca-1(10),8-diene iodide (8).
Yield 0.25 g (34%), light yellow powder. The physical
constants and spectral characteristics of the product
coincided with those reported in [17].
1H-imidazolium iodide (3). Yield 0.03 g (3.5%),
1
white powder, mp 285°C. H NMR spectrum
(DMSO-d6), δ, ppm: 0.05 s (6H, MeSi), 0.51 m (4H,
CH2Si), 0.58 m (4H, CH2), 1.66 m (8H, CH2), 2.38 s
(3H, Me), 4.05 s (4H, CH2N), 7.60 s (2H, 4-H, 5-H).
13C NMR spectrum (DMSO-d6), δC, ppm: –4.40
(MeSi), 10.64 (Me), 9.81, 26.41 (CH2), 38.05 (CH2N),
121.40 (C4, C5), 142.92 (C2). 15N NMR spectrum
(DMSO-d6): δN –199.6 ppm. 29Si NMR spectrum
(DMSO-d6): δSi 19.6 ppm.
This study was performed using the facilities of the
Baikal Joint Analytical Center, Siberian Branch,
Russian Academy of Sciences.
REFERENCES
1. Lee, S., Jeon, Y., Lim, Y., Hossain, A., Lee, S., Cho, Y.,
Ju, H., and Kim, W., Electrochim. Acta, 2013, vol. 107,
p. 675.
2-Methyl-1,3-bis[(1-methylsilolan-1-yl)methyl]-
1H-imidazolium triiodide (4). Yield 0.91 g (66%),
1
Rf 0.87 (acetone). H NMR spectrum (acetone-d6), δ,
2. Lee, J.P., Yoo, B.J., Suresh, T., Kang, M.S., Vital, R.,
and Kim, K.J., Electrochim. Acta, 2009, vol. 54,
p. 4365.
ppm: 0.27 s (6H, MeSi), 0.69 m (4H, CH2Si), 0.79 m
(4H, CH2), 1.57 m (8H, CH2), 2.81 s (3H, Me), 4.21 s
(4H, CH2N), 7.74 s (2H, 4-H, 5-H). 13C NMR spec-
trum (acetone-d6), δC, ppm: –4.44 (MeSi), 11.35 (Me),
11.00, 27.14 (CH2), 39.37 (CH2N), 122.60 (C4, C5),
143.97 (C2). 15N NMR spectrum (acetone-d6):
δN –205.3 ppm. 29Si NMR spectrum (acetone-d6):
δSi 19.8 ppm. Found, %: C 27.73; H 4.13; I 54.85;
N 4.47; Si 7.86. C16H31I3N2Si2. Calculated, %: C 27.92;
H 4.54; I 55.31; N 4.07; Si 8.16.
3. Nasr-Esfahani, M., Elhamifar, D., Amadeh, T., and
Karimi, B., RSC Adv., 2015, vol. 5, p. 13087.
4. Sheng, X., Zhou, Y., Yang, Y., Zhang, Y., Zhang, Z.,
Zhou, S., Fu, X., and Zhao, S., RSC Adv., 2014, vol. 4,
p. 30697.
5. Hu, J., Gao, F., Shang, Y., Peng, C., Liu, H., and Hu, Y.,
Microporous Mesoporous Mater., 2011, vol. 142,
p. 268.
1,3-Bis{[dimethyl(phenyl)silyl]methyl}-2-methyl-
6. Song, H., Luo, Z., Zhao, H., Luo, S., Wu, X., Gao, J.,
1H-imidazolium iodide (5). Yield 0.50 g (49%), white
and Wang, Z., RSC Adv., 2013, vol. 3, p. 11665.
1
powder, mp 265–267°C. H NMR spectrum
7. Nguyen, P., Hesemann, P., and Moreau, J.J.E.,
Microporous Mesoporous Mater., 2011, vol. 142,
p. 292.
(DMSO-d6), δ, ppm: 0.31 s (12H, MeSi), 2.02 s (3H,
Me), 3.98 s (4H, CH2N), 7.32 s (2H, 4-H, 5-H), 7.40 m
(5H, Ph). 13C NMR spectrum (DMSO-d6), δC, ppm:
–3.67 (MeSi), 10.09 (Me), 39.84 (CH2N), 122.46 (C4,
C5); 128.91, 130.95, 134.63, 135.30 (Ph); 142.53 (C2).
15N NMR spectrum (DMSO-d6): δN –206.2 ppm.
29Si NMR spectrum (DMSO-d6): δSi –2.5 ppm. Found,
%: C 52.45; H 6.04; I 24.66; N 5.18; Si 11.63.
C22H31IN2Si2. Calculated, %: C 52.16; H 6.17; I 25.05;
N 5.53; Si 11.09.
8. Karimi, B., Elhamifar, D., Clark, J.H., and Hunt, A.J.,
Chem. Eur. J., 2010, vol. 16, p. 8047.
9. Trilla, M., Pleixats, R., Man, M.W.C., and Bied, C.,
Green Chem., 2009, vol. 11, p. 1815.
10. Cazin, C.S.J., Veith, M., Braunstein, P., and Bed-
ford, R.B., Synthesis, 2005, p. 622.
11. Stathatos, E., Lianos, P., Jovanovski, V., and Orel, B.,
J. Photochem. Photobiol., A, 2005, vol. 169, p. 57.
1,3-Bis{[dimethyl(phenyl)silyl]methyl}-2-methyl-
1H-imidazolium triiodide (6). Yield 0.48 g (25%),
12. Gadenne, B., Hesemann, P., and Moreau, J.J.E., Chem.
Commun., 2004, p. 1768.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 3 2017